CS305383A2 - Method of 1-sulpho-2-azetidinone's derivatives production - Google Patents

Method of 1-sulpho-2-azetidinone's derivatives production

Info

Publication number
CS305383A2
CS305383A2 CS833053A CS305383A CS305383A2 CS 305383 A2 CS305383 A2 CS 305383A2 CS 833053 A CS833053 A CS 833053A CS 305383 A CS305383 A CS 305383A CS 305383 A2 CS305383 A2 CS 305383A2
Authority
CS
Czechoslovakia
Prior art keywords
group
protected
optionally
compound
coq
Prior art date
Application number
CS833053A
Other languages
Czech (cs)
Inventor
Shoji Kishimoto
Taisuke Matsuo
Michihiko Ochiai
Original Assignee
Takeda Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26414878&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CS305383(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from JP57073728A external-priority patent/JPS58189176A/en
Priority claimed from JP57093463A external-priority patent/JPS58210061A/en
Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Priority to CS845205A priority Critical patent/CS520584A2/en
Priority to CS856479A priority patent/CS647985A2/en
Publication of CS305383A2 publication Critical patent/CS305383A2/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Cephalosporin Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

A 1-sulfo-2-oxoazetidine derivative of the formula <CHEM> wherein R<a> is -COQ<0> (Q<0> is an amino group which may optionally be protected or substituted), -COQ<5> (Q<5> is a hydroxyl group which may optionally be protected), -(CH2)na- R<4a> (n<a> is an integer of 1 to 3; R<4a> is a hydrogen atom or a carbamoylamino, N-sulfocarbamoylamino, carbamoyl, carbamoyloxy, N-sulfocarbamoyloxy, haloalkylcarbonylcarbamoyloxy, alkylsulfonyloxy, pyridinio, alkoxy, alkylsulfinyl, alkylsulfonyl, halogenoalkylcarbonyloxy, hydroxyl, alkoxycarbonyl, acyloxy, 1-alkoxyiminoalkyl, alkylcarbony or acylamino group) or a nitrogen-containing heterocyclic group; R<1> is an amino group which may optionally be acylated or protected; and X is a hydrogen atom or a methoxy group, or a salt or ester thereof, and methods of producing said compound (I<a>) which may be shown as follows <CHEM> wherein the symbols have the same meanings as respectively defined above, and intermediates for preparing the compound (I<a>) and methods of producing them. The compound (I<a>) has improved antimicrobial and beta -lactamase-inhibitory activities and is of value as drugs for human beings and domesticated animals.
CS833053A 1982-04-30 1983-04-29 Method of 1-sulpho-2-azetidinone's derivatives production CS305383A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CS845205A CS520584A2 (en) 1982-04-30 1984-07-04 Method of 1-sulpho-2-azetidinone's derivatives production
CS856479A CS647985A2 (en) 1982-04-30 1985-09-11 Method of (z)-2-(2-amino-4-thiazolyl)-2-(esterified-carboxyimino)acetic acid's heterothioester production

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP57073728A JPS58189176A (en) 1982-04-30 1982-04-30 1-sulfo-2-azetidinone derivative and its preparation
JP57093463A JPS58210061A (en) 1982-05-31 1982-05-31 1-sulfo-2-oxoazetidine derivative, its preparation and use

Publications (1)

Publication Number Publication Date
CS305383A2 true CS305383A2 (en) 1990-02-12

Family

ID=26414878

Family Applications (1)

Application Number Title Priority Date Filing Date
CS833053A CS305383A2 (en) 1982-04-30 1983-04-29 Method of 1-sulpho-2-azetidinone's derivatives production

Country Status (22)

Country Link
EP (1) EP0093376B2 (en)
KR (1) KR840004403A (en)
AT (1) ATE51223T1 (en)
AU (1) AU564150B2 (en)
CS (1) CS305383A2 (en)
DD (1) DD212510B3 (en)
DE (1) DE3381353D1 (en)
DK (1) DK161832C (en)
ES (4) ES8505340A1 (en)
FI (2) FI831457A7 (en)
GB (2) GB2124207B (en)
GR (1) GR78189B (en)
HU (2) HU194876B (en)
IL (1) IL68451A0 (en)
MC (1) MC1513A1 (en)
MX (1) MX155085A (en)
NO (2) NO160581C (en)
NZ (2) NZ204039A (en)
PH (1) PH22251A (en)
PT (1) PT76621B (en)
SU (1) SU1480763A3 (en)
ZW (1) ZW9283A1 (en)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2515182B1 (en) * 1981-10-23 1986-05-09 Roussel Uclaf NOVEL PRODUCTS DERIVED FROM 3-AMINO 2-OXO AZETIDINE 1-SULFAMIC ACID, THEIR PREPARATION PROCESS, THEIR APPLICATION AS MEDICAMENTS AND THE INTERMEDIATE PRODUCTS NECESSARY FOR THEIR PREPARATION
FR2558467B2 (en) * 1981-10-23 1987-03-20 Roussel Uclaf NEW PRODUCT DERIVED FROM 3-AMINO 2-OXO AZETIDINE 1-SULPHAMIC ACID, ITS PREPARATION PROCESS, ITS USE AS A MEDICAMENT AND AN INTERMEDIATE PRODUCT NECESSARY FOR ITS PREPARATION
US4501697A (en) * 1983-06-17 1985-02-26 E. R. Squibb & Sons, Inc. 4-[[(Amidomethyl)oxy]methyl]-2-oxo-1-azetidinesulfonic acid salts
EP0151411A1 (en) * 1984-02-03 1985-08-14 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Antibacterial composition
EP0187500B1 (en) * 1984-12-20 1993-04-28 The Upjohn Company Monobactams
US4883869A (en) * 1984-12-20 1989-11-28 The Upjohn Company Novel beta-lactams containing amino acid substituents
US4684722A (en) * 1986-01-06 1987-08-04 E. R. Squibb & Sons, Inc. Monosulfactams
GB8614710D0 (en) * 1986-06-17 1986-07-23 Ici Plc Process
US5194604A (en) * 1990-06-29 1993-03-16 E. R. Squibb & Sons, Inc. Process and intermediates for beta-lactams having aminothiazole(iminooxyacetic acid)acetic acid sidechains
IT1244699B (en) * 1991-02-01 1994-08-08 Luso Farmaco Inst PROCESS FOR THE PREPARATION OF 3 ACYLAMINO-4- CARBAMOYLOXY-METHYL-2-AZETIDINONE-L-SULPHONIC ACIDS AND INTERMEDIATES FOR THEIR PREPARATION
AU4133697A (en) * 1996-09-23 1998-04-14 Synphar Laboratories, Inc. 3,4-disubstituted azetidin-2-one derivatives useful as cysteine proteinase regulators
AT406773B (en) 1998-04-02 2000-08-25 Biochemie Gmbh NEW SALT OF 7- (2- (AMINOTHIAZOL-4YL) -2-
EP3511328B1 (en) 2014-03-24 2021-03-03 Novartis AG Monobactam organic compounds for the treatment of bacterial infections
ES2817537T3 (en) 2015-09-23 2021-04-07 Novartis Ag Salts and solid forms of a monobactam antibiotic
EP3661933B1 (en) 2017-08-02 2022-03-23 Novartis AG Process for preparing 1-(((z)-(1-(2-aminothiazol-4-yl)-2-oxo-2-(((3s,4r)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)-1-sulfoazetidin-3- yl)amino)ethylidene)amino)oxy)cyclopropane carboxylic acid
USD994821S1 (en) 2019-02-13 2023-08-08 Hs Produkt D.O.O. Pistol
USD1071069S1 (en) 2019-02-13 2025-04-15 Hs Produkt D.O.O. Stippled textured body for a firearm or the like
USD1077123S1 (en) 2019-02-13 2025-05-27 Hs Produkt D.O.O. Firearm sight
USD1057880S1 (en) 2019-08-09 2025-01-14 Hs Produkt D.O.O. Pistol
CN111303144B (en) * 2019-12-13 2020-11-27 苏州信诺维医药科技有限公司 Compound for treating bacterial infection
USD1049292S1 (en) * 2021-04-06 2024-10-29 Springfield, Inc. Pistol
USD1069964S1 (en) 2021-11-03 2025-04-08 Hs Produkt D.O.O. Pistol slide
USD1057882S1 (en) 2022-08-29 2025-01-14 Springfield, Inc. Combined serrations for a firearm slide
USD1072997S1 (en) 2022-08-29 2025-04-29 Springfield, Inc. Firearm
USD1061781S1 (en) 2022-11-30 2025-02-11 Hs Produkt D.O.O. Pistol

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ205240A (en) * 1980-02-07 1984-07-31 Squibb & Sons Inc Sulphonamide derivatives,being starting materials for producing beta-lactams
NL8100539A (en) * 1980-02-12 1981-09-01 Rhone Poulenc Ind NEW THIOLESTERS, THEIR PREPARATION AND THEIR USE IN SYNTHESIS.
WO1982001873A1 (en) * 1980-12-05 1982-06-10 Takeda Chemical Industries Ltd 1-sulfo-2-oxoazetidine derivatives and process for their preparation
MX7096E (en) * 1980-12-05 1987-06-19 Takeda Chemical Industries Ltd METHOD FOR PREPARATION OF 2-OXOAZETIDINE DERIVATIVES
CA1262128A (en) * 1981-08-27 1989-10-03 Christian N. Hubschwerlen .beta.-lactams
DE3377061D1 (en) * 1982-06-03 1988-07-21 Hoffmann La Roche Process for the preparation of 1-sulfo-2-oxoazetidine derivatives

Also Published As

Publication number Publication date
GB2156350B (en) 1986-06-04
EP0093376A2 (en) 1983-11-09
ES8607924A1 (en) 1986-06-01
GB8509070D0 (en) 1985-05-15
GB2124207A (en) 1984-02-15
HU199115B (en) 1990-01-29
DK161832B (en) 1991-08-19
NO160581C (en) 1989-05-03
ATE51223T1 (en) 1990-04-15
FI881563A0 (en) 1988-04-05
NZ204039A (en) 1988-01-08
ES8609236A1 (en) 1986-09-01
FI831457A0 (en) 1983-04-28
ES8800186A1 (en) 1987-10-16
GB2156350A (en) 1985-10-09
FI881563A7 (en) 1988-04-05
DK161832C (en) 1992-01-20
DK188983A (en) 1983-10-31
GR78189B (en) 1984-09-26
PT76621A (en) 1983-05-01
FI831457L (en) 1983-10-31
DD212510A5 (en) 1984-08-15
ES528562A0 (en) 1986-06-01
SU1480763A3 (en) 1989-05-15
PT76621B (en) 1986-01-17
DD212510B3 (en) 1989-11-08
FI831457A7 (en) 1983-10-31
DK188983D0 (en) 1983-04-28
NO160581B (en) 1989-01-23
NZ215805A (en) 1988-01-08
ZW9283A1 (en) 1983-09-28
ES521954A0 (en) 1985-05-16
GB8310520D0 (en) 1983-05-25
NO870981D0 (en) 1987-03-10
IL68451A0 (en) 1983-07-31
NO831514L (en) 1983-10-31
KR840004403A (en) 1984-10-15
ES551942A0 (en) 1987-10-16
DE3381353D1 (en) 1990-04-26
AU564150B2 (en) 1987-08-06
EP0093376B1 (en) 1990-03-21
EP0093376A3 (en) 1986-10-15
EP0093376B2 (en) 1999-04-07
ES543809A0 (en) 1986-09-01
PH22251A (en) 1988-07-01
GB2124207B (en) 1986-10-08
HU194876B (en) 1988-03-28
MX155085A (en) 1988-01-26
NO870981L (en) 1983-10-31
MC1513A1 (en) 1984-02-10
AU1344583A (en) 1983-11-03
ES8505340A1 (en) 1985-05-16

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